Start before you're ready
There will never be a good time.
You can wait until the stars align until things seem perfect, and you can wait a lifetime.
Think about the classic situation of a kid too afraid to jump into a pool.
You know that there is nothing to be afraid of and you can try to convince them with words but it will never work, they just have to leap and find out.
You have to take the leap, sometimes that means doing things you never thought you could do.
Talking to people you never thought you could.
This kind of transgression is built into the American character.
Can you find a way to do it too?